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Publication numberUS5151453 A
Publication typeGrant
Application numberUS 07/561,194
Publication dateSep 29, 1992
Filing dateAug 1, 1990
Priority dateApr 6, 1989
Fee statusPaid
Also published asUS5334625
Publication number07561194, 561194, US 5151453 A, US 5151453A, US-A-5151453, US5151453 A, US5151453A
InventorsRobert L. Ibsen, Donald R. Pacropis, William R. Glace
Original AssigneeDen-Mat Corporation
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Light-curable ionomer dental cement
US 5151453 A
Abstract
Two-part dental cement systems based on glass ionomers which are curable on exposure to light. The dental cement systems comprise a two-part blend of sodium N(p-tolyl)glycine-glycidyl methacrylate (Na NTG-GMA) and pyromellitic dianhydride-methyl methacrylate (PMDM) resins and glass ionomers.
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Claims(11)
We claim:
1. A two-part dental cement system composed of
a. a powder comprising:
1. Alumina fluoride silicate glass
2. Barium tungstate
3. Zinc oxide
4. Equilibrium mixture of Sodium N(p-tolyl)glycine-glycidyl methacrylate (Na NTG-GMA) with NTG-GMA
5. Ethyl 4-dimethylamino benzoate; and,
b. a liquid comprising
6. Ethoxylated bisphenol A dimethacrylate
7. 2-hydroxyethyl methacrylate
8. pyromellitic dianhydride-methyl methacrylate (PMDM)
9. Polyacrylic acid
10. 2,3-bornanedione
11. Butylated hydroxytoluene
12. Benzoyl peroxide
13. Tartaric acid
powder (a) and liquid (b) being stored separately and brought into use by mixing them in (a)/(b) weight ratios of 2/1-1/1.
2. The system of claim 1 in which the components are present in the following concentrations:
1. 65-90%
2. 0-15%
3. 0.0-10%
4. 5-10%
5. 0.0-2%
6. 50-80%
7. 10-25%
8. 2.5-17%
9. 1-5%
10. 0.05-0.25%
11. 0.01-0.08%
12. 0.005-0.05%
13. 0.10-1%.
3. The system of claim 1 in which the components are present in the following concentrations:
1. 82%
2. 7%
3. 2%
4. 8%
5. 1%
6. 73.71%
7. 18%
8. 5%
9. 3.1%
10. 0.14%
11. 0.03%
12. 0.02%
13. 0.12%.
4. A two-part dental cement system composed of:
a. a paste comprising:
1. Alumina fluoride silica glass
2. 2-hydroxyethyl methacrylate
3. Ethoxylated bisphenol A dimethacrylate
4. Equilibrium mixture of Na NTG-GMA with NTG-GMA
5. Zinc oxide
6. Barium tungstate
7. Ethyl 4-dimethylamino benzoate; and,
b. a paste comprising:
8. Alumina fluoride silica glass
9. 2-hydroxyethyl methacrylate
10. Ethoxylated bisphenol A dimethacrylate
11. 2,3-bornanediol
12. Butylated hydroxytoluene
13. Benzoyl peroxide
14. Polyacrylic acid
15. pMDM
paste (a) and paste (b) being stored separately and brought into use by mixing them in an (a)/(b) weight ratio of about 1/1.
5. The system of claim 4 in which the components are present at the following concentrations:
1. 18-60%
2. 5-15%
3. 20-50%
4. 5-15%
5. 0.0-15%
6. 0-15%
7. 0.0-2%
8. 25-65%
9. 5-15%
10. 20-50%
11. 0.05-0.30%
12. 0.005-0.10%
13. 0.005-0.05%
14. 1-5%
15. 2.5-17%.
6. The system of claim 5 in which the components are present in the following concentrations:
1. 48%
2. 7%
3. 27%
4. 8%
5. 2%
6. 7%
7. 1%
8. 57%
9. 7%
10. 28%
11. 0.1%
12. 0.05%
13. 0.01%
14. 3%
15. 5%.
7. A dental cement comprising the powder and liquid described in any of claims 1-3 mixed in a powder/liquid weight ratio of 2/1-1/1.
8. A dental cement comprising the pastes described in any one of claims 4-6 mixed in a paste (a)/paste (b) weight ratio of about 1/1.
9. A method for treating a tooth, the method comprising applying a cement according to any one of claims 7 and 8 to the tooth and then curing the cement.
10. The method of claim 9 wherein the curing is done by exposing the cement to light.
Description
CROSS REFERENCES TO CO-PENDING APPLICATIONS

This is a continuation of U.S. Ser. No. 07/333,904, filed Apr. 6, 1989, now abandoned.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to dental cements It is more particularly directed to light-curable dental cements based on glass ionomers.

2. Description of the Prior Art

Ionomer cements are a recent advance in the practice of dentistry. Some of the better of such compositions are described in U.S. Pat. No. 4,738,722 to Ibsen, Glace and Pacropis. These cements have excellent adhesion and give minimal pulpal trauma, but tend to cure rather slowly, a disadvantage in many dental procedures.

SUMMARY OF THE INVENTION

The cements of this invention have all the advantages of the cements described in the Ibsen patent, and in addition, provide enhanced physical strength and bonding, but most importantly, have the ability to cure instantly on exposure to light.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

The cements of the present invention are a two-part system, each part of which can be packaged separately for storage and sale. These parts are mixed together just before use, thus insuring a fresh and vigorous cement.

There are two embodiments of the cements from which a dentist can choose, the selection depending on the viscosity needed. The first is a power/liquid, whose viscosity can be varied according to the powder/liquid ratio used when the powder and liquid are mixed. The second is a paste/paste, whose viscosity will be fixed when the pastes are mixed.

All cements of the present invention have the same components, whose concentrations will of course vary according to the viscosities desired.

These components are:

1. A glass. Any of the types customarily used in cements of this type can be employed, but a preferred type is that from which fluoride ions are leached. A glass which is especially preferred is an alumina fluoride silica glass made by Specialty Glass Company of Oldsmar, Fla., and designated SP912-1 Glass.

2. Barium tungstate.

3. Zinc oxide or titanium dioxide.

4 A bonding agent. As with the glass, any of those ordinarily used in cements of this type can be used, but those preferred for use are:

NTG-GMA--alone or n combination with the sodium or other alkali metal salt of NTG-GMA. This material is made by the Esschem Corporation and believed to have the structure. ##STR1## PMDM--also made by Esschem Corporation and believed to be a pyromellitic dianhydride extended with methyl methacrylate.

5. Ethyl 4-dimethylamino benzoate.

6. Ethoxylated bisphenol A dimethacrylate.

7. 2-hydroxyethyl methacrylate.

8. 2,3-bornanedione.

9. Butylated hydroxytoluene.

10. Polyacrylic acid, polymaleic acid, polyitaconic acid, or a copolymer of acrylic acid, maleic acid or itaconic acid. These polymers should have molecular weights Mw of 3000-250,000, and can be easily prepared by conventional techniques. This component preferably contains about 5% of d-tartaric acids.

11. Benzoyl peroxide.

Components 2, 3, and 5-11 are commercially available.

The first embodiment of the present invention, the powder/liquid two part system, has the following composition:

Powder

Glass 65-90% by weight, preferably about 82%

Barium Tungstate 0-15%, preferably about 7%

Zinc oxide 0.0-10%, preferably about 2%

Equilibrium mixture of Na NTG-GMA with NTG-GMA 5-10%, preferably about 8%

Ethyl 4-dimethylamino benzoate 0.0-2%, preferably about 1%

Liquid

Ethoxylated bisophenol A dimethacrylate 50-80%, preferably about 73.71%

2-hydroxyethyl methacrylate 10-25%, preferably about 18%

PMDM 2.5-17%, preferably about 5%

Polyacrylic acid (or other polymer) 1-5%, preferably about 3.1%

2,3-bornanedione 0.05-0.25%, preferably about 0.14%

Butylated hydroxytoluene 0.01-0.08%, preferably about 0.03%

Benzoyl peroxide 0.005-0.05%, preferably about 0.02%

Tartaric Acid 0.10-1%, preferably about 0.12%

The powder and the liquid are made by mixing the listed components, in any order, under ambient conditions. To prepare the system for use, the powder and the liquid are mixed at a powder/liquid weight ratio of 2/1-1/1, as determined by the viscosity desired of the cement product.

The second embodiment of the present invention, the paste/paste two-part system, has the following composition:

Paste A

Glass 18-60%, preferably about 48%

2-hydroxyethyl methacrylate 5-15%, preferably about 7%

Ethoxylated bisphenol A dimethacrylate 20-50%, preferably about 27%

Equilibrium mixture of Na NTG-GMA with NTG-GMA 5-15%, preferably about 8%

Zinc oxide 0.0-15%, preferably about 2%

Barium Tungstate 0-15%, preferably about 7%

Ethyl 4-dimethylamino benzoate 0.0-2%, preferably about 1%

Paste B

Glass 25-65%, preferably about 57%

2-hydroxyethyl methacrylate 5-15%, preferably about 7%

Ethoxylated bisphenol A dimethacrylate 20-50%, preferably about 28%

2,3-bornanedione 0.05-0.30%, preferably about 0.1%

Butylated hydroxytoluene 0.005-0.10%, preferably 0.05%

Benzoyl peroxide 0.005-0.05%, preferably about 0.01%

Polyacrylic acid (or other polymer) 1-5%, preferably about 3%

PMDM 2.5-17%, preferably about 5%

The pastes are made by simply mixing the listed components, in any order, under ambient conditions. To prepare the system for use, the pastes are mixed in a paste A/paste B weight ratio of about 1/1.

MODE OF OPERATION

The dentist uses the system by combining the powder and liquid of embodiment 1, or the two pastes of embodiment 2, in the ratios desired, and then mixing them. The resulting cement is then applied to a tooth as needed, according to recognized principles of dental practice. The cement will self-cure in about 20-30 minutes, but cures instantly on exposure to light. Light having a wave length of about 480 nM at an intensity of about 5000 foot-candles is preferred. A exposure of about 30 seconds is sufficient to cure the cement in most applications.

Various modifications can be made to the present invention without departing from the apparent scope hereof.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US4659751 *Feb 3, 1986Apr 21, 1987American Dental Association Health FoundationSimplified method for obtained strong adhesive bonding of composites to dentin, enamel and other substrates
US4674980 *Sep 22, 1983Jun 23, 1987Den-Mat, Inc.Dental composite and porcelain repair
US4746686 *Apr 17, 1987May 24, 1988Kerr Manufacturing CompanyVisible light activated cavity liner
US5084491 *Mar 16, 1989Jan 28, 1992The Ohio UniversityReinforcing glass ionomer dental filling material with stainless steel, or metals thereof
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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US5445823 *Oct 20, 1994Aug 29, 1995The Procter & Gamble CompanyDermatological compositions and method of treatment of skin lesions therewith
US5593303 *Oct 21, 1994Jan 14, 1997Cohen; MortonAttachment of orthodontic brackets
US5683249 *Mar 22, 1995Nov 4, 1997Den-Mat CorporationDental implant process and treated prosthetic
US5767170 *Apr 30, 1996Jun 16, 1998Den-Mat CorporationDental adhesive comprising an unsaturated monomer, a coupling agent, a crosslinker, leachable fluoride and a photoinitiator
US5847020 *Jun 6, 1997Dec 8, 1998Den-Mat CorporationDental adhesive comprising a homogeneous mixture of an unsaturated monomer a coupling agent a crosslinking agent and a photoinitiator
US5859089 *Jul 1, 1997Jan 12, 1999The Kerr CorporationDental restorative compositions
US5876743 *Sep 22, 1997Mar 2, 1999Den-Mat CorporationBiocompatible adhesion in tissue repair
US5883153 *Jul 15, 1997Mar 16, 1999Shofu Inc.Fluoride ion sustained release preformed glass ionomer filler and dental compositions containing the same
US5965632 *Jun 20, 1997Oct 12, 1999Scientific Pharmaceuticals Inc.Dental cement compositions
US6031016 *Sep 18, 1998Feb 29, 2000Den-Mat CorporationDental adhesive
US6063832 *Oct 11, 1996May 16, 2000Sankin Kogyo Kabushiki KaishaMethod of setting a dental cement composition
US6127451 *Dec 15, 1998Oct 3, 2000Kerr CorporationDental restorative compositions
US6306206Jan 6, 2000Oct 23, 2001Ultradent Products, Inc.Temporary dental cement compositions and related methods and systems
US6391286Nov 17, 1995May 21, 20023M Innovative Properties CompanyUse of metallofluorocomplexes for dental compositions
WO1996003936A1 *Aug 7, 1995Feb 15, 1996Leonard Morris SpofforthDental system
WO1997002328A1 *Jul 2, 1996Jan 23, 1997Den Mat CorpNovel dental adhesive
WO1997018792A1 *Oct 10, 1996May 29, 1997Minnesota Mining & MfgFluoride-releasing compositions
WO1998046197A1 *May 20, 1997Oct 22, 1998Minnesota Mining & MfgDental compositions with improved handling capabilities
Classifications
U.S. Classification522/14, 524/443, 523/115, 523/116, 524/406
International ClassificationC08F2/44, A61K6/083, C08F2/50
Cooperative ClassificationA61K6/083, A61K6/0835
European ClassificationA61K6/083, A61K6/083M
Legal Events
DateCodeEventDescription
Mar 18, 1996FPAYFee payment
Year of fee payment: 4
Mar 20, 2000FPAYFee payment
Year of fee payment: 8
Mar 30, 2004FPAYFee payment
Year of fee payment: 12
Mar 30, 2004SULPSurcharge for late payment
Year of fee payment: 11
Sep 5, 2007ASAssignment
Owner name: DEN-MAT HOLDINGS LLC, CALIFORNIA
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:DEN-MAT CORPORATION;REEL/FRAME:019781/0024
Effective date: 20070822
Owner name: DEN-MAT HOLDINGS LLC,CALIFORNIA
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:DEN-MAT CORPORATION;REEL/FRAME:019781/0024
Effective date: 20070822
Dec 12, 2007ASAssignment
Owner name: DEN-MAT HOLDINGS, LLC, CALIFORNIA
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:IBSEN, ROBERT;GLACE, WILLIAM R.;REEL/FRAME:020234/0091
Effective date: 20071119
Jan 2, 2008ASAssignment
Owner name: DYMAS FUNDING COMPANY, LLC, AS ADMINISTRATIVE AGEN
Free format text: SECURITY AGREEMENT;ASSIGNOR:DEN-MAT HOLDINGS, LLC;REEL/FRAME:020299/0955
Effective date: 20071213
Nov 15, 2011ASAssignment
Owner name: DEN-MAT HOLDINGS, LLC, CALIFORNIA
Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:DYMAS FUNDING COMPANY, LLC;REEL/FRAME:027226/0873
Effective date: 20111114